


Overthinking With My Heart

by minthalo



Category: IT (Movies - Muschietti), IT - Stephen King
Genre: Age Difference, Alternate Universe, Alternate Universe - No Pennywise (IT), Alternate Universe - Sugar Daddy, Anal Sex, Blow Jobs, Bottom Eddie Kaspbrak, Daddy Kink, First Time, Gay Eddie Kaspbrak, Gay Richie Tozier, Getting Together, I Want That Twink Obliterated, M/M, Possessive Richie Tozier, Sugar Daddy, Top Richie Tozier, age gap, its two am as i post this im tired and yearning, sugar baby eddie, sugar daddy richie, thigh fucking
Language: English
Status: Completed
Published: 2020-01-08
Updated: 2020-01-08
Packaged: 2021-02-26 01:02:07
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 20,498
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21794995
Author URL: https://archiveofourown.org/users/minthalo/pseuds/minthalo
Summary: Eddie Kaspbrak, 21Looking for nice conversation and help with rent.I’m not willing to do anything I regret, message me first if interested.Eddie's a broke college student who needs help with rent, Richie's a lonely comedian looking for nice conversation, neither of them are on a seeking arrangements site looking for anything serious, especially not love
Relationships: Ben Hanscom/Beverly Marsh, Eddie Kaspbrak/Richie Tozier
Comments: 80
Kudos: 901





	Overthinking With My Heart

**Author's Note:**

> This fic. has taken me so long to write, and is longer than originally expected  
> Anyway im a huge slut for sugar daddy aus and there was a severe lack of the specific type that i like in this fandom so i rolled up my sleeves and wrote it myself
> 
> special thank yous to em [sunxcherries ](https://archiveofourown.org/users/sunxcherries) for helping me come up with a title and figuring out the summary and amber  
> [Rainbowsandgucci ](https://archiveofourown.org/users/rainbowsandgucci) for the help with the mood board on the tumblr post that you can find [here](https://minthalo.tumblr.com/post/190136698739/overthinking-with-my-heart-20k-eddie-kaspbrak) as well as yelling at me constantly to get this done, without you two this fic would have been nothing but an idea lost to time
> 
> Hope you enjoy!

Eddie sits awake in his bedroom at two in the morning, his roommates asleep in their own rooms across the hall. Eddie, however, came home from work roughly an hour ago, they had a rough close on top of a sales floor meeting, so he got out of work half an hour later than expected, and had to take the long way home, his usual bus route was closed for the night.

He crosses his legs in his desk chair, forcing himself to concentrate on his Econ homework due the next morning. He rubs his face, and rolls back his shoulders, he wanted to get this done before he left for work at the department store that day, but his other job at the small bakery down the street had him pick up a morning shift. He didn’t want to take a shift there, but he could definitely use the boost in his paycheck.

All Eddie wants to do is fall backwards into bed, wrap himself in a blanket burrito and stay there until the end of the semester. His mind continues to wander off as he doodles in the margins of his notebook, ever since he cut his mom off at the end of the summer he’s been having to financially support himself, at first he didn’t think it would be so bad, but working two jobs and barely making rent on time on top of his student loans and having to feed himself, it’s a nightmare.

He thinks back to a conversation he heard the day before between two girls sitting in front of him during his introductory accounting course. One mentioned how she was getting paid to have dinner with an older man that night, and showed pictures of the other men she met through an arrangement website full of older men looking for young people to keep them company.

Eddie slides his econ book over and opens up his phone, typing in the name of the website his classmate said. She implied that she was doing more than just holding a conversation with them, but at this point Eddie doesn’t care, he’ll do anything if it means he can go down to one job, and not be up at odd hours of the night attempting to do homework.

He downloads an app that looks secure enough, with quality reviews, when looking it up online in the websites information section it states that they provide background checks on each member, regardless of age, to ensure they’re a real person, and with the “sugar daddies” of the site they send current bank statements to prove they can provide what the “sugar babies” are asking for.

Eddie makes himself a “sugar baby” profile, and setting his preferences to men. He adds a few pictures, making sure any picture he puts up are only of himself, his friends faces either strategically cropped out or not in at all. He keeps his bio is simple and honest.

Eddie Kaspbrak, 21

Looking for nice conversation and help with rent. 

I’m not willing to do anything I regret, message me first if interested.

He makes his profile public and swipes through the men on the app, not interested in most of them. He doesn’t focus on their looks, he doesn’t care about that, he isn’t planning on sleeping with them. Most of them are significantly older than him, over double his age, but he doesn’t care at this point, he swipes right on just about any of them that don’t explicitly say that sex is a requirement for them.

Eventually he puts his phone down and pulls his econ book back to the center of his desk, forcing himself to finish the homework and read the rest of the chapter before crawling into his bed around four in the morning. 

Eddie sleeps through his alarms and wakes up ten minutes before his first class of the day. He grabs his backpack off his desk chair and runs out of his apartment, having no time to pee much less check his phone for potential messages. He has back to back classes until 2pm, only then is he able to write down all the assignments he needs to have finished by the end of the day and make his way home.

He falls onto his couch and closes his eyes, taking a short nap, waking up when Beverly and Bill come home from their own classes. He sits up and rubs his face, realizing he slept two hours and he still has homework to do.

“Hey Eddie, we brought you some food.” Beverly sits next to him and hands him a styrofoam box from the school’s cafeteria.

He grins and opens it, taking a fork from her hand, “thanks, you’re the best.” 

“You look exhausted, what time did you get to sleep last night?” Bill asks, plopping himself in the armchair near him.

“Around four” Eddie wipes his mouth, “I had so much Econ homework to do, and I got distracted halfway through it and spent half an hour trying to look for an older man to pay my bills for me, but eventually I got it done.”

“Excuse me?” Beverly snatches the fork out of Eddie’s hand, earning her a whine, “no, no. You’ll get this back after you explain yourself, you were looking for an older man to do what?”

Eddie huffs, “I heard some girls talking about going on dates with older men and getting paid for it, and I was so frustrated, it was two am, I was running on red bull and tears, so I made a profile and swiped on some men. I didn’t talk to anyone, I haven’t even checked the app to see if I matched with anyone, I probably won’t.”

Bill laughs, “I don’t blame you, but this can be dangerous, and gross. You don’t know who you’re matching with, or what kind of diseases they have.”

Eddie takes his fork back from Bev, pushing her away from his food, “I didn’t want to do anything sexual, I put that in my bio, I just want a free meal and to not have to work two jobs, it’s dreaming I know.”

“You never know,” Beverly says, putting her legs on Eddie’s lap, only to have them pushed off immediately, “If you do make sure your location is on, and tell us when.”

“I will, I will, you track me anyway so it won’t be an issue.” He finishes up his meal and grabs all his trash, “I better do my homework now, I have to open at the bakery tomorrow.” 

Bill sighs, “come out if you have the time, we never get to see you anymore.”

“We miss you, Eddie.” Beverly reaches out.

Eddie squeezes her hand and lets it drop back onto her lap, “Believe me, I know.”

Eddie doesn’t end up opening the app until around seven in the evening, he’s gotten just about all of his homework done so he allows himself to lay back on his bed and take a breather. He’s matched with almost everyone he swiped on, that alone gives his ego a bit of a boost. 

A lot of the messages start by asking him what’s off limits, or if doing anything sexual is part of something that he’ll regret, he unmatches with those men quickly, not giving them the time of day. 

He talks with a man in his early fifties, he isn’t very attractive but Eddie doesn’t care. The conversation lasts maybe ten minutes before the man sends him a picture of his dick without any warning, needless to say Eddie unmatches with him as quickly as his fingers will let him.

He’s about to give up hope when a thirty four year old man messages him, he clicks on his profile to refresh his memory before he opens the message.

Richard Tozier, 34

Call me Richie.

Entertainer.

Looking for someone to make conversation with, nothing more is necessary.

The pictures added are of a very attractive older man, his hair is a bit shaggy, curling at the ends with a few gray hairs sprinkled throughout. He has a nice smile with light blue eyes that Eddie finds not threatening, which is all he really wants in one of these men.

Richie’s message to him is simple and straight to the point.

Richie: **I’ll take nice conversation and won’t make you do anything you’ll regret.**

Eddie looks at it for a few moments before messaging him back.

Eddie: _Something i’ll regret also includes unsolicited dick pics so if thats on ur mind move on to someone else._

Richie: **Woah what who actually sends those**

Eddie: _Multiple people started out with some and one guy i talked to for like 10 minutes sent one without any warning_

Richie: **Holy shit gross**

Eddie: _yeah so please none of those_

Richie: **That wont be a problem you don’t have to worry about it**

They message back and forth for a little while longer before Richie brings up the topic of seeing each other in person to discuss this being a real arrangement, making a point to say Eddie will be compensated for the date, even if it doesn’t go anywhere.

They make plans for Friday evening, it gives Eddie time to go to work at the bakery and come home to prepare himself for the date. Richie makes the reservation after they set a proper time and tells him he looks forward to seeing him that night.

Eddie looks up the place once he sends his final good night texts and his eyes go wide, it isn’t the fanciest place around but it’s better than anywhere he would even think of going. He plans his subway route so he’ll get there safe and stands up to plan his outfit, even though it’s only Monday, and the date isn’t until Friday, Eddie doesn’t like being unprepared.

They message back and forth on the app for a few days, conversation topics lasting for days, Eddie isn’t able to text back often between work and school, and it seems like Richie is the same way, he doesn’t answer unless it’s early in the morning or late in the day, occasionally during midday but nothing too often.

Eventually Friday evening comes around, Eddie had a shift at the bakery early in the morning, arriving home a bit after eleven in the morning. He drops everything on his desk and crawls into bed, waking up around three in the afternoon.

Eddie rolls over in his bed and opens his phone, seeing a message in the app from Richie, reminding him of their date, telling him he’s looking forward to seeing him. He sits up and rubs his face, both Bill and Beverly are working closing shifts, he won’t see them until the end of the day.

He sends a message in their group chat with Beverly’s boyfriend, Ben, that he’s going on a date with a potential sugar daddy, telling them the name of the restaurant and making sure they all can track him. 

They send back a variety of messages, Ben tells him to be safe, Bill tells him to make sure he has an escape route in case it doesn’t go as planned. Beverly tells him to ‘have fun, get fucked’. Eddie fondly rolls his eyes and texts them a thank you before putting his phone down.

He begins to pick up his room, his mind running a mile a minute, cleaning his messy room is a nice distraction. He’s able to get his floor cleared off, make a nice pile of laundry that needs to be washed as well as clear off his desk so he can do his homework without feeling crowded.

He leaves his door open to air out his room a bit more and puts on the outfit he planned days ago, a nice button up shirt tucked into black jeans, he hopes he isn’t under dressed, he debates for a solid half an hour, pulling out other shirts and debating wearing dress pants before he settles on his original outfit, putting everything he threw around his room back on their respective hangers, hanging them up in his closet.

After he has his minor freak out he grabs his phone, wallet, and apartment keys, and leaves, locking the door behind him. Eddie already mapped the subway route he’s going to take, if everything is on time, which he knows it won’t, the only consistency about the NYC subway is that there is no consistency.

Eddie arrives in front of the restaurant ten minutes later than expected, which is fine with him, he gave himself a twenty minute leeway. 

He takes a deep breath and pushes open the door to the restaurant, only to realize it’s actually a pull, and steps back to let himself in, hoping no one saw him struggle right then. Walking up to the hostess he relaxes a bit, the other guests are dressed about as well as he is, so he really had nothing to worry about.

Eddie mentions his name and the reservation to the Hostess, she smiles and takes him to a table near the back of the restaurant. Eddie looks around and makes note of where the restroom is located, as well as how far away the door is. 

Richie sits up when Eddie is seated in front of him and gives him a smile as the Hostess hands him his menu. 

The first thing Eddie notices about him is the large glasses framing his face, and the light blue eyes behind them. The second is that he’s wearing a dark blue hawaiian shirt with a white t-shirt underneath.

“Hey, Eddie. I’m glad you made it.” 

Eddie sits back in the chair, “me too, I mean, I’m glad you made it too…”

He shifts, it feels awkward, they haven’t really talked much over text, and that was easy, but in person it’s different, so different. Eddie looks down at his hands, he told himself appearances don’t matter, he isn’t doing anything sexual with him, but Richie is much more attractive in person than he was on his profile.

Richie clears his throat and lifts up the menu, “I didn’t know if you wanted anything to drink, so I just left it with water.”

Eddie looks up and smiles, “water is fine, that’s good.”

“Good…” He trails off.

They sit in silence for a bit longer, the only noise coming from the light music playing, and chatter from tables around them. 

Eddie shifts, uncomfortable with the atmosphere, “So, your bio on the app said you were an entertainer, what exactly does that mean?”

“Oh, I’m a comedian.”

“Really? What kind of comedy?”

Richie looks at him for a moment, it’s clear he’s thinking about something specific, but isn’t saying anything out loud. His demeanor shifts after that, he relaxes a bit more, sitting back in his chair.

“Stand up mostly, I do shows in bars around the city, sometimes outside of it.”

Eddie smiles, “Woah, that’s really cool, it must be hard to find gigs around here, I’m sure it’s a competitive market.”

“Yeah, yeah I guess it kind of is, but I like doing it.”

“That’s good, something that makes you happy.”

“It is, yeah. So what are you in school for?”

The conversation moves on from there, not more stumbles or awkward silences, the two of them getting increasingly more comfortable with each other. Richie makes a few jokes that has Eddie covering his mouth, saying between laughs “y-you can’t just say stuff like that!”

Of course Richie doesn’t stop saying stuff like that, he really likes the way Eddie laughs, the crinkle of his eyes, his head tipping back and delicate hands covering his mouth. 

They trade phone numbers as they eat dinner, Eddie deletes the app after he makes sure he has Richie’s number, he isn’t going to meet with anyone else, he knows that for sure, even if it doesn’t work out with him, he’ll take that as a sign and suffer with both his jobs.

Once the two of them are done with their meal Richie pulls out an envelope and sets it in front of him. 

He sits back, “I guess we should talk arrangements now.”

Eddie nods, letting his hands fall onto the table, tabbing his fingers lightly, “yeah, we can talk about that now.”

“If you want to continue this, and have it be a regular thing, I can set something up for you, but I need to know if you want this.”

Eddie nods again, maybe a little too hard, “y-yeah, I’d like this to be a regular thing, dates like this, with my work and school schedule it might be a little hard, and we’ll have to do lunches sometimes but I’d like to.”

“That’s fine, we’ll make time, we don’t have to figure that out now, we can talk about it later, here’s the money for today.” Richie hands him the envelope, Eddie takes it and sets it in his lap. “I was thinking I’ll set up a bank account for you, you’ll have access to it, and can do whatever you want with the money that’s in there, and after every date you’ll get a cash bonus.” 

Eddie looks inside the envelope, counting out two hundred dollars in twenties. He looks up and tilts his head.

“You want to give me an allowance on top of this? Isn’t this more than enough?”

“Think of the allowance as a reason to keep talking to me. At our next date I’ll have the account set up, and give you access to it.”

Eddie nods, “Yeah, that sounds good to me.”

“Your allowance can be like, four hundred a week?” Richie asks, like the number he threw out wasn’t well over Eddie’s weekly department store paycheck. 

“Y-yeah, that sounds great.” He agrees, maybe a little too quickly, he’s sure he probably could have haggled a bit, got Richie to pay him more, but what he’s getting is already more than enough. 

Richie pays for their meal and stands up, walking Eddie out of the restaurant, “Text me when you get home, so I know you’re safe.”

Eddie grins up at him, “yeah, yeah, for sure. I’ll send you my schedule for the next week, so we can set up another date.”

Richie nods and Eddie walks away, it seems a little weird for him to just leave his date outside the restaurant instead of giving him at least a hug goodbye, but that wasn’t a real date, and Richie is just a man paying him for his company.

Eddie texts Richie that he’s home safe as he walks into his apartment, closing and locking the door behind him. He puts his phone in his back pocket and walks into the living room, draping himself over Ben and Beverly’s laps as they watch a movie.

Ben pauses the movie as Beverly pushes Eddie onto the floor. He lands with a thump and a laugh, lifting his head up with a large smile.

“Well someone looks happy, how was your arrangement?”

“It was fucking great, this might be way better than I expected.” Eddie pulls himself up and sits on the couch, “we’re going to meet again later next week, he’s really nice, and funny too.”

“Yeah, what’s he look like?” 

Eddie pulls out his phone only to frown, “I deleted the app, I got his phone number so I don’t have his profile saved anymore. His name is Richard, dark hair, blue eyes, he’s cute, and kinda young, well not really young, he’s thirteen years older than me, but that’s a small gap compared to most of the men on that app.”

“Thirteen years is still a lot.” Ben says.

Eddie shrugs, “he’s my sugar daddy, nothing else, but I’m not gonna lie, he’s kinda hot, in that older man way, but I don’t know him that well.”

He stands back up and stretches, “I’ll let you two be alone, I’ll see you in the morning.” 

Eddie shuts his bedroom door behind him and strips off his clothes, putting on a pair of sweatpants before getting under the covers, it’s not so late that he can fall asleep, but it’s late enough that he can get comfortable in bed, he doesn’t have work tomorrow, but it means he has to play catch up with homework for all four of his classes.

He pulls out his phone and texts Richie his schedule for the next week so they can set up another date.

Eddie: _I have class from 9am-2pm and work 4-10:30 mon/wed and work 4:30-11am and have class from 3-7:30pm on tues/thurs we can do dinner on tues or thurs or i can do friday after my morning shift_

Richie: **holy shit kid do u ever sleep**

Eddie: _sometimes. not much tho_

Richie: **how many hours a week do u work???**

Eddie: _i try to get 40 total. it hard tho they dont wanna give me more than 28 a week_

Richie: **thats fucking ridiculous you shouldnt have to work that much on top of a full school schedule**

Eddie: _rent in nyc b like that 🤪✌🏻_

Richie: **well I hope i can help out with that. How does a next friday lunch sound?**

Eddie: _sounds great_

The rest of Eddie’s week is pretty uneventful, it’s work, school, home, rinse and repeat. The one thing that really motivates him is Richie, texting him quickly becomes a highlight to his days. He becomes more comfortable with their conversations, he knows the next date they have it won’t be nearly as awkward as the first one.

Eddie goes straight from work at the bakery to the lunch spot Richie picked across town, it’s not an issue for him, he doesn’t mind taking the subway to meet up with him. 

When he arrives he can see Richie sitting inside by a window, scrolling on his phone, Eddie grins and walks inside, taking a seat across from him.

Richie grins and sets his phone down, “Hey, Eddie, I was just about to text you, there was this couple walking down the street with a baby stroller, but inside the stroller was a french bulldog.”

Eddie laughs, “there is no way you just saw that.”

“No, no, I did, worst part is I know the couple, it was my friend John and his wife.” He shows him a picture he took of the two of them through the window.

John Mulaney is standing in front of the window, flicking Richie off while his wife presses her face in her hands.

“Holy crap, you know John Mulaney?” Eddie says, his eyes going wide, “My friends watch his Netflix specials, like, all the time.”

Richie laughs, putting his phone down, “yeah, I do. Comes with working in the business, you get to know big name comedians like him. I worked with him on SNL for a while.”

“That’s really cool, I didn’t know you did stuff like that, you must know a lot of really famous comics.”

Richie smiles, like he’s holding back another laugh, “yeah, I do, I don’t think of them as famous, mostly I think of them as assholes”

Eddie laughs and sits back in his chair, he takes a look at the menu, looking over it for a while, not sure what to get.

“The reuben is really good here, I think you’d like it, most people do.”

Eddie looks up and sets the menu down, “yeah? That sounds pretty good right now, I’m running on two cups of stolen iced coffee and a croissant that fell off the tray at work, so I’m starving.”

Richie scrunches up his nose, “Gross, don’t eat floor food.”

Eddie shrugs, “It didn’t land on the floor, I’m not an animal, I caught it but squished it in my hand, I wasn’t able to serve it. I’m not going to pay three dollars for a croissant, even with my thirty percent off discount.”

“You only get thirty percent off for working there?”

“Yup, it’s a scam, I know. I never really follow it, I’ll bring my own cup and get iced coffee and tell them I brought it from home. It’s like a little mom and pop shop, the owner is always there when I walk in at four thirty, making freshly baked pastries. I set everything up, like pull down tables and chairs, count the cash drawer, turn on all the lights, and set up the display case, stuff like that.”

“Still, you’re working full shifts for them and you don’t even get a free drink?”

“Please, If they had it their way they wouldn’t give me any discount, they’re irritated already that they have to pay me fifteen an hour, New York is one of the only states that has their minimum wage that high.”

“You make fifteen an hour and still have to work two jobs?”

“Yeah, look where we live, I have two roommates and rent is still sixteen hundred a month, I mean that’s a lot lower than the other places we were looking at though, so I guess I’m lucky it’s not the three of us crammed in one studio apartment.”

“You shouldn’t have to be thankful that working two jobs means you can barely pay rent every month.”

Eddie shrugs, “it is what it is, but you don’t have to worry about it.” He reaches across the table and gives Richie a smile.

The waitress walks over and Richie orders for the two of them without thinking. Eddie doesn’t say anything, it’s kind of nice to have someone else take over for you.

As she walks away Richie pulls out his wallet and hands Eddie a bank card. Eddie takes it and looks it over before taking his hand from Richie’s and putting it in his own wallet. 

“I can use this for whatever I want?”

“Yeah, it’s yours,” Richie hands him a small business card, “I had them write some information down so you could download the app for it and check its balance, this way you know what’s on the card at all times.”

Eddie takes the card and pulls out his phone, setting up the app right there so he doesn’t have to worry about it later. Once he has it set up he sees that Richie put in two weeks worth of allowances.

“We’ve been talking for about two weeks now, I figured I could start off with that. I have it hooked that every Sunday it’ll put in four hundred into your account, so you don’t have to worry about when you’ll get paid.”

“Thanks, this is great.” Eddie says, looking down at his phone.

The rest of the lunch goes well, Eddie loves the reuben and eats the entire thing, on top of the fries that came with it, in less than fifteen minutes.

“Damn, you weren’t kidding.” Richie laughs, still working on his own sandwich.

He shrugs, “I told you, I haven’t eaten all day.”

Eddie makes conversation with Richie as he finishes up his own meal, getting the check and paying for the both of them. Eddie still feels a little awkward letting someone else pay for his meal, but he can see himself getting a bit more comfortable with this whole arrangement eventually.

“I can let you go if you’re too tired, you did get up pretty early for work today.” Richie says as they walk out of the building.

Eddie shakes his head, “no, I won’t be able to sleep now that I’ve eaten, I’m way to riled up, we can keep talking, let’s walk.” 

Richie leads him down the sidewalk, they have to walk close together with everyone passing them by from the opposite direction.

Eddie doesn’t mind it, the other man's body heat welcome, it’s only mid September but the weather is already colder than Eddie is prepared for, with just a thin long sleeve shirt on. While Richie rambles on about something that Eddie was originally paying attention to, but now can only focus on how cold his hands feel, he shivers, bringing his arms up.

Richie, without putting much thought into it, takes off his leather jacket while he talks, putting it around Eddie’s shoulders. Eddie looks up, cheeks slightly pink, Richie tells himself it’s because of the wind.

“You’re shivering, I don’t need the jacket, you do.” He says simply, squeezing Eddie’s shoulder, letting his arm linger around him for a bit longer than necessary. Eddie slips his arms through the sleeves and inhales, it smells like Richie’s cologne.

They spend another half hour walking across the town, eventually Eddie recognizes the area they’re in and leads them to his apartment building. 

“I hope you didn’t drive to the restaurant because we’re a ways away from it now.” Eddie says, stopping in front of the door.

Richie shakes his head, “I called an Uber, don’t worry, thanks for letting me talk for so long.”

“Thanks for dinner, and everything else that came with it.” Eddie says, fiddling with the sleeves of the jacket before slipping it off.

Richie takes the jacket, their hands touching for just a moment, and in that split second Eddie makes a decision. 

He stands on his toes and gives Richie a kiss on the cheek. Richie smiles so bright that Eddie can’t help but lean back in and give him a soft kiss to his lips before backing up, thanking him for the date once again.

Richie stands outside of the building for almost a full minute, stunned. His hand comes up to his cheek, then touches his lips before he lets himself smile again. He slips his arms through his jacket and walks down the street, calling himself an Uber.

Eddie lays in bed that night staring at his ceiling, his mind running a mile a minute as he thinks about his day. The date was great, Richie made him laugh a lot, unknowingly walked him back to his apartment, he gave him his jacket to keep him warm, but most importantly, he gave him a total of a thousand dollars. Four hundred each week, plus two hundred for the date that day. 

That thousand dollars is more than Eddie has in his savings account. Getting a sugar daddy is absolutely the best decision he’s ever made. If they continue to go on weekly dates he’d be getting six hundred dollars a week, that’s more than his combined paychecks, if Eddie does this for a while, which he most definitely plans on doing, he’s set to quit one of his two jobs.

The department store is definitely the one he’ll choose to quit, working there is a nightmare. The long hours late into the night keep him riled up so he never falls asleep on time, working closing shifts and then being forced to open at the bakery the next morning is terrible. Working at the bakery is not the perfect job, but it’s miles above working for a corporation.

He rolls onto his side and grabs his cellphone, texting the general manager at his job.

Eddie: _This is me putting in my resignation. The last schedule posted today are the last shifts I’ll work here_

It’s not the most professional thing he could have done, but Eddie doesn’t care at this point, that job was like living a nightmare, they were always short staffed and he was doing multiple peoples jobs at once, on top of terrible customers that would follow him around the store to tell him how he’s doing his job wrong, and managers that expected way too much out of someone working minimum wage.

Eddie has a short conversation with his manager after he replies, thanking him for giving him the working opportunity, when he’s asked why he’s leaving he tells him he found a new job opportunity where he’s able to move up.

It’s a straight up lie but he’s not about to tell his married forty year old manager with two kids that he’s leaving because he found a sugar daddy.

He sleeps nice and easy that night, the stress slowly lifting off his shoulders, just one more week where his schedule is awful, then he’ll be able to hang out with his friends more, focus on school, or at the very least, be able to get a full eight hours of sleep.

The following Thursday Richie picks Eddie up from his last shift at the department store to take him out for ice cream. Eddie wanted to to a proper date but he doesn’t have the time, he has huge projects in two of his classes due in the next week, this is the only free time he has.

Richie doesn’t mind it, spending a few hours with Eddie late at night is better than nothing at all.

The two of them get their bowls of ice cream and Richie drives them out to a park outside the city, in more of a secluded area so they’re alone. He pops open the bed of his truck and they sit on top of it, Eddie swinging his legs as he licks the ice cream off his spoon.

“How was your last day at the department store?” Richie asks.

“It was amazing, but literally nothing could have made it a bad day, a customer could have dumped their hot coffee on my head and I still would be like ‘this was an amazing day!’”

Richie laughs, “seriously?”

“Yes! I don’t have to work two jobs anymore! As soon as I turn in these projects next wednesday I’ll have all the time in the world to do whatever I want! Whatever I want will be trying to make the dean's list so I can keep my scholarship, and seeing my friends more than the twenty minutes between me leaving and them coming home, and really it’s all thanks to you.”

Eddie leans over and presses a kiss to Richie’s cheek. He smiles and looks down at him, he can’t help the warm feeling that covers his chest now that Eddie is more comfortable with him. Touches like that were not a requirement for him at all, and they definitely weren’t expected of him, but they’re nice now that he’s voluntarily doing them.

Richie talks about his work for a bit, saying that he’s preparing for a show in a few weeks, so he’s spending most of his time writing material and running it by his two friends, Stan and Mike. 

Eddie finishes his ice cream and sets down his empty bowl next to him, wiping off his mouth with a napkin before stuffing it in the empty bowl. He enjoys listening to Richie talk about his work, it’s an interesting side of the world Eddie would never normally have an insight to, going to school for economics and all.

Eddie watches him talk for a moment, focused on his mouth, he’s got a bit of ice cream on his bottom lip that he hasn’t noticed. After a few minutes of Richie not doing anything about it, Eddie scoots a bit closer, so their knees are touching, and leans in, kissing the ice cream off his lip.

Richie’s hand comes up to cup his cheek, closing his eyes and kissing back, he tries to pull away after a moment but Eddie only moves closer, pulling his legs up and placing a hand on Richie’s shoulder.

Richie’s other hand finds its way to his hip, he allows himself to kiss back, feeling Eddie press closer and closer, almost climbing into his lap.

“Hey, hey, slow down, baby.” He mumbles against his lips, pulling his head back a bit.

Eddie makes a small noise when the pet name slips out, “don’t want to.”

Richie shifts, getting a bit more comfortable while Eddie takes this as an opportunity to straddle his lap. He laughs lightly and squeezes his hip as Eddie settles down, wrapping both arms around Richie’s neck.

He leans in for another kiss, Richie indulges him for a bit longer, until Eddie grinds down in his lap, making another tiny noise against his mouth. Richie pulls away, pulling Eddie’s head back by a light grip on his hair.

“You keep making noises like that and we’re going to have an issue.” Richie says, a bit breathless.

“Won’t be an issue if you let me take care of it.”

Richie swallows, “hey, we talked about this, you don’t have to do it, it’s not a requirement.”

“I want to.” Eddie insists, “I do.”

“Eddie.” Richie says, rubbing his face, trying to think clearly. “Don’t feel like you have to, seriously.”

“But I want to, I really want to.” Eddie presses a bit closer, rolling his hips.

Richie squeezes his side, keeping him still, “Fuck, okay.” He lets go of his hip and has him slip off his lap.

They end up in the back seat of Richie’s pickup truck, it’s spacious enough for the two of them to fit back there, not exactly comfortably, but nothing is digging into anyone's bones. Richie spreads his legs and Eddie nestles between them, unbuttoning his jeans, pulling them down just enough to pull Richie’s dick out.

Eddie licks the palm of his hand, getting it wet before wrapping it around Richie’s cock, jerking him slow. He leans up and kisses him again, a bit more desperate than before.

Richie groans against his mouth, his hand cupping his cheek, “fuck, baby.”

He mewls at the pet name, enjoying it far more than he probably should. Eddie speeds up a bit, feeling him slowly harden in his hand, he swipes his thumb over the tip, hearing Richie let out a quiet moan, deep from the back of his throat.

Eddie pulls back to breath, touching his nose to Richie’s for a moment before sitting back completely. He looks over the man in front of him, licking his lips. 

He scoots back in the seat, as far as he can, there really isn’t much room for both of them to be doing this. He looks up, locking eyes with Richie as he leans in, wrapping his lips around the tip of his cock.

Richie reaches down, threading his fingers through his hair, “Eddie- god.” He tips his head back, his Adam’s apple bobbing as he swallows dry.

He swirls his tongue around the tip, pulling back to lick down the shaft, closing his eyes, the taste isn’t terrible, it’s actually quite pleasant. 

Richie is a lot bigger than anyone else Eddie’s been with, which isn’t many other people, but he feels like he should have expected it, with the size of Richie’s hand compared to his own.

Eddie bobs down, taking in another few inches, jerking what he can’t fit in his mouth. He knows his own limits, he won’t be able to take all of Richie in his mouth, even though he would love to, just to hear more of his quiet curses.

“Fuck- shit baby, your mouth is so hot, feels so good, Eddie.”

He moans quietly around him, just hearing him talk turns him on, he shifts, his pants beginning to get uncomfortably tight.

Eddie moves his hand out of the way and tries to take a bit more in his mouth, only to choke on the length. Richie pulls him back by his hair, a thin line of spit connecting the tip of his cock to Eddie’s lip.

“Don’t take too much baby, you don’t have to choke on my cock to do a good job.”

Eddie nods, pulling away from his grip to dip his head back down. He feels Richie’s hand controlling his movement now, so he doesn’t take too much in, he moans around his cock, the feeling of someone else using his mouth, even if it’s to prevent him from choking himself, is so hot.

It’s barely another minute when Richie pulls him off his dick completely, “gonna come, baby.” He groans out.

Eddie opens his mouth wide, sticking his tongue out, using his hand to finish him off. “Come on my face, daddy.” 

Richie groans, coming in streaks, painting Eddie’s face with his come. Eddie jerks him through it, licking off anything that’s close enough to his mouth.

Richie pulls Eddie up and kisses him, nearly shoving his tongue into his mouth. His arms wrap around Richie’s shoulders, grabbing at the nape of his neck.

Eddie moans and ruts his hips against him, “D-Daddy, please.” He whines against him.

“Shhhh, baby, I got you. Did such a good job for me.” Richie unbuttons Eddie’s shorts, pulling out his dick, jerking him a few times before Eddie comes with a cry in his hand, scratching his upper back lightly.

They spend a few moments to calm down from their high, their kisses getting less desperate and more relaxed until they stop altogether., Eddie resting his forehead on Richie’s breathing heavy.

He pulls back and tucks himself back in his pants, Richie reaches down and finds some old napkins to wipe off his hands, and Eddie’s face, getting at anything he wasn’t able to get with tongue.

“You don’t have to call me daddy you know.” Richie breaks their silence, gently cleaning off Eddie’s cheeks.

Eddie hums, closing his eyes, letting himself enjoy his soft touch. “I know, but I wanted to, felt right, it was hot.” He leans in for another kiss, not able to get enough of his lips.

Richie cups his cheek again, thumb gently touching just under his eye, “It was hot, you’re hot, baby.”

“I like that too, the pet names, it’s nice to hear those instead of just ‘Eddie’.”

“Then I’ll keep ‘em coming, princess.”

Eddie flushes at that one, and as Richie’s face blossoms into a large grin, he instantly feels regret. 

Eddie walks into his apartment that night way later than he planned with a satisfied smile along with a hundred dollar raise in both his allowance and date ‘compensation’. 

Richie’s sitting on the couch alone in his apartment, writing some new material for a stand up show that’s planned a few weeks from then, he has notebook papers scattered all around him, his phone in one hand while his ipad sits in his lap, his laptop on the coffee table in front of him, everything around him having jokes and bits he tries to fit together in a way that properly flows.

He is minding his own business, completely enveloped with his own writing, when his two best friends bust down his front door, using their own key to let themselves in without being invited, or informing Richie before hand that they’re here.

Richie looks up from his laptop, seeing Stan and Mike standing over him, “uh, can I help you?”

“You.” Stan points at him, “you smiled yesterday. Today, you talked to your agent without pitching a fit, you agreed to add new show dates, you’re actually going through with this show in a few weeks, and you have new, _good,_ material written, what’s different?”

Richie sits back sliding his ipad next to him, “why does something have to be different?”

“Because we know you, Rich.” Mike says, sitting next to him, “last month you argued with me for even hinting at new shows being in your future, you stopped writing your own material since your recorded show last year, you didn’t even want to leave the house. It’s like in the last month a switch has been flipped, you don’t have to hide things from us, you know.”

Richie shifts, taking a deep breath, “Okay, don’t get mad, I mean, you were going to have to find out eventually, Mike specifically, ‘cause the whole you being my manager thing, and it’s kind of a bad thing, well, maybe not a _bad_ bad thing, but it’s not a great thing.”

“Oh my god, Richie what have you done?”

“I’m a sugar daddy. I have a sugar baby, just one, his name is Eddie, he’s twenty one, so legal, I’ve been seeing him for a little under a month now.”

Stan relaxes significantly, “Oh, okay. That’s not too bad, I mean the thirteen year age gap isn’t the greatest but I’m not on your PR team so it’s not my problem, and this explains the mysteriously missing funds from your personal checking account.”

“However, as your manager, I’m part of your PR team.” Mike speaks up, watching his face, leaning back against the couch, “Sugar baby, huh, just that?”

Richie nods, “uh, yeah, yeah. He’s in school for economics, lives in an apartment with two of his best friends. He’s cute, and funny, so sweet, and nice. He was working two jobs when I met him, not anymore, he’s so thankful to me that he doesn’t have to anymore.”

Richie talks about Eddie for a bit longer, his eyes shine in a way that Mike hasn’t seen in months, he has this gentle expression on his face that makes Stan soft, seeing his friend finally find something that makes him happy, makes him want to keep moving on.

“I mean, I’m only his sugar daddy, this isn’t anything more to him, and it’s all temporary, but I really don’t care.”

Stan nods, “I get it, this could be good for you.”

Mike puts a hand on his shoulder, squeezing gently, “Besides, you never know, yeah?”

Richie nods, and the conversation moves on from there. Mike and Stan stay for the rest of the day, helping him with his new material, Mike finding his way into the kitchen to cook Richie a proper dinner.

At the end of the night the trio find themselves back on Richie’s couch, all under blankets with crumpled up pieces of rejected material around them.

“So, back on the topic of Eddie,” Stan starts, sitting up, “these expenses once a week, you giving him his ‘allowance’ or whatever, I’ll write off as personal expense, yeah? You don’t want the federal government to know you have a sugar baby.”

Richie looks over at him, pointing in his direction, “Write them off as-”

“Beep beep, Richie.”

“I didn’t even say anything!”

“Yeah, but you were going to.”

Richie can’t deny that.

Eddie walks into his apartment on a Wednesday afternoon after his classes for the day. He kicks off his shoes and leaves them by the door in a pile next to Beverly’s boots, and makes his way into the living room, dropping his backpack next to the couch and laying across it, resting his head on Bill’s lap.

Bill laughs lightly and pushes him up, “get off me, you loaf.”

Eddie laughs and swipes at Bill’s hands, shifting so he can get comfortable just sitting next to them. He pulls his legs up and crosses them on the couch, smiling at the armchair where Beverly sits curled up with Ben.

“How was class?” Ben asks.

“It was alright, nothing eventful happened.”

“No work tonight?” Bill asks, already knowing the answer.

Eddie’s face splits into a large grin, “No work at nights ever again!”

“Finally, now you can actually hang out with us.” Beverly says, “We miss you, loser.”

“You don’t have to miss me anymore, I’m going to be around you guys so often you’ll be begging me to pick up more shifts.”

“Please, if you would never voluntarily work more now that you don’t desperately need the cash, and if you do ever need money you can just call up your sugar daddy.” Bill pushes at his shoulder.

“Oh shut up, you’re just jealous all I have to do to make three hundred dollars is go out with him for a free dinner.”

“And a blowjob, can’t forget that.” Ben sing-songs.

Eddie flushes a light pink down to his neck, “shut up, it won’t be a regular thing, maybe. I don’t know.”

“I don’t see a problem with it, I told you on your first date to get fucked, and now you’re halfway there.” Beverly shrugs.

“He’s like forty years old and paying Eddie to just talk to him, who knows what kind of skeletons are in his closet.” 

“He’s thirty four, not forty, and he’s really sweet. He just wants nice conversation, he told me in the beginning that sex wasn’t a requirement, now can we please stop talking about this.” Eddie nearly begs, staring at his lap.

“Fine, fine.” Bill rolls his eyes, “We’ve been watching a bunch of comedy specials on Netflix while you were in class, rewatched John Mulaney’s Kid Gorgeous, now we’re watching this guy, his name is Richie Tozier.”

Eddie’s head snaps up at the name, sure enough on the TV in front of him is Richard Tozier, his sugar daddy. He’s dressed similar to the way he is on their dates, a nice pair of jeans with a Hawaiian shirt over a plain T-shirt. 

His mouth feels dry, he swallows, trying not to make it too obvious that he recognizes the man in front of him. 

“He calls himself Trashmouth, it’s hilarious.” Ben says, grabbing the remote to start the show back up.

Eddie slips out his phone, pulling up his messages, looking at his friends to make sure none of them are looking in his direction, all three watching the special.

Eddie: _WHY DO YOU HAVE A NETFLIX SPECIAL????_

Richie: **I told you I do standup this is my job eddie**

Eddie: _u told me u were a comedian not a professional like this!!! Wtf!!!!!_

Richie: **you didnt know this already? Eddie come on im not that underground im not underground at all**

Eddie: _i dONT HAVE TIME TO GOOGLE I JUST TOOK UR WORD !!!!!!!_

Richie: **how did you think i could afford to keep you around lol**

Eddie: _idk i assumed u were living off family money or smth not a LITERAL CELEBRITY?????_

Richie: **family money lmao. why are you only finding this out now?**

Eddie: _my friends r watching ur netflix special rn. The one called trashmouth_

Richie: **oh yeah that came out last year. Dont tell them but i have another one coming out within the next year/eighteen months**

Eddie: _this is too much a literal celebrity is my sugar daddy_

Richie: **have you told them about me?**

Eddie: _they know i have a sugar daddy not that my sugar daddy is celebrity Richie Trashmouth Tozier. i probably wont tell them at all if they find out they find out but it wont be coming directly from me_

Richie: **this is really messing with your head isnt it**

Eddie: yes.

Richie: **dress up nice tonight. im making a reservation.**

“Eds, you good?”

Eddie looks up to see Ben and Beverly looking at him, both with confused expressions crossing their faces.

“Uh, yeah.” Eddie clears his throat, sitting up straight, “My, uh, my sugar daddy, he’s a bit more successful than I thought he was.”

“Is that an issue?” Bill asks.

He shakes his head, “no, I don’t think it will be. Well it might be, can you guys help me pick out an outfit for tonight? He’s taking me somewhere and told me to dress up nice.”

The next day Eddie mentions in a text that going to such a fancy restaurant in a shirt he got on the clearance rack at Walmart made him feel a little out of place, especially with Richie sitting across from him, wearing such higher end brands like they’re nothing.

Their next date Richie takes him to his own personal tailor, getting him fitted for more than a few nice dress shirts, made with such a nice material Eddie could cry when he feels it touching his bare skin. Along with those shirts he gets him a fitted suit, that makes his ass look amazing as Richie put so delicately. 

Eddie repays him with a heated make out session in his truck, parked in an empty parking lot leading into a nature trail a few blocks away from his tailor. Richie shoves him into the back seat, nipping and biting at his neck until Eddie comes in his pants, scratching Richie’s back through his shirt.

Two weeks after there Eddie is working at the bakery, it’s been a relatively slow morning for a Friday, but it’s still early, 6:30 in the morning, they’ve been open for an hour and have only had a handful of people come in, the rain outside deterring most from leaving so early. He hums to himself, he finished his homework for the weekend the night before, so other than a morning shift on Sunday, he plans on doing absolutely nothing this weekend. 

Saturdays have become set “date night” days with Richie, they spend most of the day with each other, he’ll pick him up for an early dinner and he won’t get home until well after midnight, Richie taking him to his apartment every night, making sure he gets home safe.

Eddie trusts Richie a lot more than he did at the beginning of their arrangement, he allows Richie to pick him up and drive him around, he doesn't always text his roommates when he’s on a date, not as fearful that Richie will murder him. 

The sexual aspect doesn’t always come up, but Eddie is in his twenties, he’s always horny on main. Everything they’ve done is hand or mouth stuff, the two of them in the backseat of Richie’s truck.

The nights they do that Eddie is compensated for it, but he doesn’t really care about the extra money for that, he’d be perfectly okay if it stayed the same. Sometimes during the week they’ll see each other again, either out to lunch or just a walk in the park together. Eddie looks forward to them, he genuinely enjoys being around him.

The pet names are more frequent now, and Eddie can’t deny the little flutter in his stomach every time Richie calls him baby, and he knows Richie loves when he calls him daddy, the almost possessive look in his eyes every time he says it.

He can tell Richie is holding back, but no matter how hard Eddie pushes he’s stopped before they get any further. 

Their date for this week has been called off, Richie actually has a show a few hours away, he’s leaving soon, and has been texting Eddie all morning complaining about how early it is, asking how the hell he does this every couple days.

Eddie’s on his knees behind the display case, properly plating the croissants that just came off the tray, now cool enough to be served to customers. The bell attached to the doorframe rings when the door is opened, he groans quietly to himself, irritated someone would have the audacity to walk in the store during the hours that they are open.

As he stands back up he sees two men walking inside, one he immediately recognizes as Richie. He ducks back down quickly, taking a deep breath, they were talking to each other, neither noticed he was even there. He’s the only one in the store at the moment, the owner stepping out to take a business related phone call, he knows he won’t be back for a while. 

Eddie rubs his face and decides to play it as cool as he can, standing back up, “Hello, welcome to Blueberry Bakery, can I interest you in any of our fresh baked chocolate chunk cookies? They’re currently buy one get one free.”

Richie makes eye contact with him, staring in silence for more than a few moments, enough for Stan to recognize the tension between them, it’s not exactly awkward but it’s definitely uncomfortable, for him at least. 

“Uh, I think we’re good on cookies, but those croissants smell good.” he walks up to the counter. “Can we get two of those, and a pumpkin muffin?”

“Yeah, of course, would you like those packaged to go?” Eddie stays, slipping on a pair of gloves to grab them from the trays on the cooling rack.

“Yeah, three hot coffees too, we have a long drive ahead.” Stan says as Mike walks in, shaking his head off from the rain.

Richie collects himself and hip checks Stan out of the way as he’s getting out his wallet, taking out his own card and handing it to Eddie.

“Hey, I can pay for my own coffee, Richie.” Stan grumbles.

“Yeah, I’m sure you can, but I’m Rich, it’s in the name.” He grins.

Eddie snickers to himself, swiping the card and hands it back before turning around and pouring them three cups of coffee, leaving room for cream in Richie’s without being asked, knowing how he likes it already. 

He sets two of the coffees on the counter, handing Richie his, “creamer is on the table behind you.” he says softly.

Richie smiles, their fingers touching for a bit longer than necessary. “Thank you.”

Eddie ducks his head with a soft smile and turns around going back to replating the pastries. Mike picks up the bag of baked goods, watching Eddie curiously for a moment, before looking back at Stan who shakes his head, clearly he has something figured out that Mike does not.

On their way out Richie slips more than plenty into the tip jar on the counter, quietly so Eddie doesn’t notice.

The moment the door to the bakery shuts Stan clears his throat, “that was him, wasn’t it?”

“Yeah, that was Eddie.” He says softly.

Mike nods, connecting the two dots as they make their way to the parked car waiting for them. “He’s pretty cute, for a twenty year old.”

“He’s twenty one, and he’s adorable, did you see how cute he was in that little apron?” Richie all but shouts, throwing his arms in the air as he talks.

Stan laughs and takes the coffee from his hand, “don’t spill this, dumbass, you need it for the day we’re about to have.” 

“I’m not done talking about him, his customer service voice is so cute, I just wanted to lean over and pinch his cheeks, so cute!”

Mike shakes his head fondly, “get in the car, you can talk about him all you want then.”

After their dinner date that following Saturday, they take a short walk in the brisk autumn, so cold it might as well be winter already, weather. It ends with the two of them going to Richie’s penthouse apartment to warm up for a bit.

Eddie has never been inside his apartment before, so once inside and after his chills are gone he spends most of his time walking around, touching anything Richie will let him, and looking inside empty rooms. 

He discovers Richie’s office that’s so cluttered with ripped up pieces of paper and books all over the floor it nearly gives him a heart attack. The spare bedroom is much more to Eddie’s liking, the bed is made proper, there’s nothing cluttering up the dresser, and nothing on the floor.

Richie leaves him to do what he wants, not having anything that he doesn’t want Eddie to find. He makes the two of them cups of hot chocolate, as adorable as Eddie’s little red nose is, he wants him to be comfortable. 

When the two drinks are completed he finds Eddie in his bedroom, sitting cross legged on his California King sized bed. He sets the two mugs down on his side table and climbs onto the bed with him, pulling Eddie close by his waist, kissing the back of his neck.

Eddie squirms in his grip, turning so he can lift his head up and kiss him proper. He pulls back after a few and touches his nose to Richie’s cheek, “What were you doing?”

Richie shifts to prop himself against the headboard, getting comfortable before he grabs a mug of hot chocolate and hands it to Eddie. “Thought you might want this, it’ll warm you up.”

Eddie smiles, “so sweet, thank you, Daddy.” He kisses his cheek before settling next to him, taking a sip.

Richie turns the TV on and the two sit in a comfortable silence for a while, Eddie doesn’t have work in the morning, so he can stay out as late as he wants, not having to force himself to go to bed at a certain time. 

He sets the mug on the nightstand when he’s done drinking it, curling into Richie’s side after, resting his head on his chest. He hears Richie set his own mug down, and feels his warm hand rest on his lower back, petting gently.

Eddie lifts his head up and kisses Richie’s jaw gently, moving up to kiss his lips. He feels him smile against him, encouraging him to keep going. Richie’s hand moves to his hip, squeezing softly. Eddie breaks the kiss to straddle his lap, wrapping his arms around his neck and pressing as close as he can when he dips his head down for another kiss.

The kisses get deeper, more intense, Richie’s other hand slips down, grabbing his ass. Eddie whines, grinding down on his lap, whimpering in his mouth, gripping his shoulders tight.

“Daddy, I want more tonight, want you to fuck me.”

Richie chokes, breaking the kiss and looking Eddie over, he’s flushed in the face down to his neck, pupils blown up with desire he can hardly seen the brown in his eyes anymore. 

“Baby, are you sure that’s want you want?”

Eddie nods, “yes, yes, I want this, I’ve wanted this, please fuck me, Daddy.”

Richie captures Eddie’s lips in a rough kiss, not able to help himself hearing him almost beg to get fucked, grinding in his lap. He wraps an arm around his back and rolls them over, Eddie’s head on his pillow, Richie hovering over him.

Eddie’s hands find their way under Richie’s shirt, touching his bare chest. He pulls back and lifts off his shirt, throwing it to the side of his bed before doing the same for Eddie. He dips his head down and kisses his neck, trailing them down to his chest.

He nips lightly, careful not to leave a mark, they’ve never gotten that far, he doesn’t want to upset Eddie by leaving a big purple hickey on his neck. 

“How do you want to do this?” Richie asks, leaning back up for another kiss to his lips, his hands unbuttoning Eddie’s pants, “how do you usually like it?”

Eddie hums, “whatever you want, I’ve never gotten this far with anyone.”

Richie breaks the kiss and pulls back, leaving Eddie to whine, trying to follow his lips.

“What do you mean you’ve never done this before? Eds are you a virgin?”

Eddie shrugs, “I guess, I mean I’ve done some other things with guys, I’ve gotten around just, not very far.”

“Are you sure you want your first time to be with me? Shouldn’t it be special, with someone you really like.”

“I like you.” Eddie sits up, wrapping his arms around his shoulders, his fingers playing with the bit of hair that falls on the back of his neck, “besides I doubt your first time was so perfect.”

“Uh, well, no it wasn’t. I lost my virginity in the back of my old pickup truck to a guy that I knew for less than a week.”

Eddie snorts, “See, it doesn’t have to be special, I don’t care, I just know I want you right now.” 

“Yeah, yeah, so you’ve said, such a needy baby boy.” Richie tips his head down and kisses him again, gently pushing him back so he’s laying flat on the mattress again. 

He finishes unbuttoning Eddie’s pants and pushes them down his thighs, breaking the kiss so Eddie can kick them off along with his underwear. He presses soft kisses down his neck and chest, flicking his tongue over his nipples. Eddie gasps, his hands grasping at Richie’s shoulders.

Richie peppers a few more kisses down, dipping his tongue into his navel to hear a sweet whimper before pulling back completely. Eddie shifts to get a little more comfortable, and watch the older man.

Richie kicks off his pants and underwear, getting them out of the way before he opens the small drawer in the bedside table and pulls out a small bottle of unscented lube with a condom. Eddie spreads his legs as Richie makes his way back, getting comfortable between them. 

Richie slides his hand up Eddie’s thigh, “I’ll be gentle, I’ll take good care of you baby.” 

Eddie bites his cheek and rests his head on the pillow, staring at the ceiling, “I trust you.”

Richie pops open the bottle of lube, he pours some across his first three fingers, warming it between his fingers before leaning up and kissing Eddie gently, getting him to relax a bit more before pressing the tip of his index finger to his hole. 

Eddie mewls softly as the rest of the finger goes in, Richie going as slow as he can manage, not wanting to accidentally force Eddie to take too much, and hurt him in the process. He presses kisses to his lips, jaw, down to his throat, licking the dip in his collarbone.

“Daddy,” Eddie moans, threading his fingers through Richie’s hair, “you can leave a mark.”

An image flashes through Richie’s mind, Eddie spread out on the bed in front of him, small red and purple marks trailing from his neck down to his stomach and thighs, looking positively delightful, and very much like Richie’s.

He almost chokes at the thought, “you sure, Kitten?”

“mmhm, I’m sure,” Eddie says, a little breathy, “I want them.”

Richie dips his head and sucks a light mark into his collarbone, he hears Eddie moan above him, blunt nails gently scratching at his back, any harder and he’ll leave a mark of his own. He leaves another a bit higher up, much lighter than the first, it’ll fade by the time morning comes. 

He presses in another finger while he kisses him again, earning another soft moan. Eddie continues to make little noises as he spreads the fingers inside of him, he tries to hold some of them back, but Richie doesn’t let him, nipping at under his jaw, encouraging any sound he can get from him. 

Richie keeps everything soft, distracting him with kisses, and little nips across his chest when he adds a third finger, taking his time stretching him. Eventually Eddie whines pulling at Richie’s shoulders, “Daddy c’mon, fuck me now, I’m ready, I can take it.”

Richie presses a sweet kiss to his lips before pulling his fingers out, he picks up the condom, trying to open it a few times, the lube on his fingers making it difficult. Eddie sits up and takes it from him, ripping it open and pulling the condom out.

Richie sits back and Eddie shifts just a bit more so he can roll it on him, jerking him a few times once it’s on. He’s already hard, clearly fingering Eddie did more than a little something to him.

“Good like this, baby?” Richie asks, lining himself up, wanting to make sure he’s comfortable in this position. 

Eddie nods, “yeah, yeah. I like being able to see you.”

Richie dips his head down and kisses him, letting him relax before pushing the tip in, starting almost painfully slow, but not wanting to hurt Eddie by accidentally starting too fast. He pauses when he’s pushed to the hilt, pressing his nose to Eddie’s neck, taking a deep breath.

“Fuck.” Eddie moans, rolling his head over, “fuck, Daddy.”

“Shhh, baby, I got you.” 

“You’re- fuck, god I knew you were huge but holy shit. This is so much bigger than my own fingers.”

Richie chokes, lifting his head up, the mental image of Eddie finger fucking himself, imagining it is Richie’s cock is too much, he can’t help but rock his hips.

“Is this what you think about when you’re touching yourself, kitten? Imagining it’s really my cock filling you up, making you feel this good?” He pulls back, starting with small thrusts.

Eddie nods, “fuck- god yeah, I wanted this for so long. I can take more, c’mon Daddy, harder, please.”

Richie kisses him again, slipping his tongue in when Eddie gasps from a particularly hard thrust. Eddie scratches at his back, his moans melting into Richie’s mouth. 

It takes a few minutes but Richie’s able to change the angle of his thrusts just enough to hit Eddie’s sweet spot every time, hearing him almost scream in pleasure is enough encouragement to go harder, faster.

Eddie squirms a lot, Richie has to hold him down, two hands on his hips, pressing him into the bed, not enough to leave any bruise, but enough that Eddie is constantly aware of his hands, he likes it a lot, maybe a little too much. 

“Daddy, m close.” He slips one hand from around Richie’s neck to his bicep, gripping tightly.

“I got you, baby, Daddy’ll take care of you.” He takes one hand off his hip, shifting to get it in between their bodies, wrapping a hand around Eddie’s hard cock.

Eddie moans, trying to buck up into his hand on instinct before Richie’s other hand presses harder, holding him down. Richie jerks him in time with his thrusts, when he swipes his thumb over the tip he’s gone, coming over Richie’s hand with a long moan.

Richie can only handle another few thrusts before he’s coming into the condom, groaning right next to Eddie’s ear.

They take a few moments before Richie pulls out, slow, a gentle hand on Eddie’s hip to settle him. He pulls off the condom and ties the end, getting up to throw it away in the bathroom trash can.

Eddie closes his eyes, his hands resting at his sides, taking deep breaths to come down from his high. He hears the water run in the bathroom, moments later feeling a warm wet cloth on his stomach.

Looking down he sees Richie cleaning him up, wiping the come off his stomach, and lube from between his thighs, careful on his ass, not wanting to touch too much where it’s sensitive. He takes the cloth back to the bathroom, leaving it on the sink before getting back into bed with Eddie, pulling him close as he pulls the covers around them.

Eddie snuggles into his chest, pressing a kiss to the skin before resting his head, closing his eyes.

Richie smiles, petting his side as he gets them proper comfortable under the covers, “Sleepy puppy.” He says softly.

Eddie hums softly, opening his mouth for a reply, but falling asleep before he can form the thought.

Eddie walks into his apartment the next day with a slight limp, warm inside remembering the events of the night before. The morning he spent there was nice, he woke up to the smell of Richie making pancakes in his, too large, kitchen. After a small make out session and a shower to get the syrup off of the places syrup definitely should not be, Richie dropped him off at his building, sending him off with a sweet kiss that lasted just a bit longer than normal.

He’s met with Beverly and Bill standing at the big window that looks out to the street in front of their apartment, Bill holding binoculars, Bev holding a phone with Ben on facetime, all three of them with increasing levels of shock on their faces.

“Uh, is everything okay-” He’s cut off by Bill’s screaming.

“Your sugar daddy is Richie fucking Tozier?”

“Eddie, holy shit, why didn’t you tell us?” Ben asks, his voice coming through with a bit of static, bad connection. 

“How big is his dick, I need to know.” Beverly demands.

“Okay, okay, I have explaining, I know, here it goes.” Eddie takes a pause before continuing. “Yes, Richie Tozier my sugar daddy-” He’s cut off once again by the three of them screaming, all asking their own questions, each one more outlandish than the last, Beverly constantly asking about his dick size.

“Will you all shut up! Beverly, his dick is none of your business! I didn’t tell any of you because I didn’t know how to react that I’m shacking up with not only someone who is significantly older than me, but is also a public figure! I’m pretty sure he’s not even out yet, he doesn’t need anyone outing him as someone who pays a young man for sex.”

“Pays for company, the sex is just a bonus.” Ben points out.

Eddie rolls his eyes, “tell that to the extra two hundred dollars in my pocket and the pain in my ass.” 

“Eddie, please, I can’t stress this enough, how big is his dick?” Bev nearly yells at him.

Bill rolls his eyes and ignores her, “Really though, did you not trust us enough to keep this kind of secret? We’re your best friends.”

“Yeah, you are.” He shifts his weight from one leg to the other, “I don’t know, I should have told you. I guess I was just overwhelmed or something, scared maybe, things are weird, he’s not my boyfriend he’s my sugar daddy, it’s not like at some point I’m going to bring him over to meet my friends, I won’t meet his parents or anything.”

Beverly sighs, dropping her very important dick question for a bit, “yeah, I guess I get it, if I was fucking a public figure like Richie Tozier I wouldn’t want it to get out either, something like that could put a huge dent in their career, especially if sexuality is involved.”

“it’s not that I don’t trust you guys, because I do, I trust you all with my life, I was just being extra cautious, ya know?”

“yeah, I get it.” Bill nods, understanding where he’s coming from a bit more after the explanation. 

“Me too, sorry we pressured you like this.” Ben tells him, feeling a bit guilty now.

“Thanks for understanding, I’m gonna go lay on the couch now, my ass hurts.” Eddie says, not even trying to hide the fact that he's limping.

“Wait, you were serious about the ass comment?” Ben yells.

“Oh my god, Eddie, _please_ , how big is his dick?”

A few days later Eddie finds himself on the couch doing homework, snapping bored selfies to Richie. He forced him to get a snapchat shortly after they started seeing each other, sending pictures through text was too much work if he was already sending the same ones on snapchat to his friends. 

Bev walks out of her room and plops herself next to Eddie, resting her head of freshly washed, wet hair on his shoulder, watching his phone. He grimaces and pushes her off.

“Stop it, you’re getting me wet.”

She laughs and crosses her legs on the couch, “was that Richie?” 

He nods, “yeah, he’s at a meeting with his managers, setting up a future tour for him, he’s bored out of his mind.” He tilts his phone to show her the photo, Richie with his head tilted back, tongue out of his mouth, playing dead.

She laughs, “I’d be bored too, just thinking about having a two minute meeting with my advisor makes me wanna choke, I don’t know how he does that.”

“Neither do I.” Eddie shifts, brushing off a red strand of hair and placing it into Bev’s lap. “This is yours.”

She rolls her eyes, “you never used to care when my hair was all over you, but now you buy all these fancy clothes and it’s a problem.”

“I didn’t buy these clothes, Richie got them for me.”

“Damn, really? Maybe I should get a sugar daddy to buy me clothes.”

“I don’t know if Ben would be too fond of that.”

“He wouldn’t be, but he doesn’t have to worry, I would never actually do it. Speaking of Richie though, you never told me how sex with him was.”

Eddie flushes, ducking his head, “Bev…”

“Come on! The first time I slept with Ben I busted down your bedroom door and screamed to you for almost three hours, you can’t leave me hanging like this.”

“Okay, okay. It was nice, like _really_ nice. He was soft, and sweet, it didn’t feel like a chore I was doing to get paid more, and I didn’t feel dirty after, not even a little. He kept it slow for me, and any time I got nervous he would slow himself down, he took his time with everything, fuck Beverly it was literally amazing.”

Bev smiles, bumping his shoulder, “Good, when you said you slept with him, I was a little worried at first, I know you said he’s a good guy but that was before I knew who he was, and men are disgusting, I know that first hand.”

Eddie nods, “you’re sweet for worrying, but really, he is a good guy, and everything was great, he was sweet and gentle, very respectful, and my ass doesn’t even hurt anymore.”

She laughs and pushes at his shoulder, “as long as you can walk.”

Eddie’s phone buzzes and he picks it up, showing Beverly the snapchat Richie sent of a terrible double chin photo, holding up a scribbled out script. Eddie laughs, smiling at his phone, eyes crinkled at the edges.

Bev watches him for a moment, “huh.” she says out loud to herself. Eddie doesn’t hear it, too focused on sending back his own snap.

The next few weeks are a flurry of stay-in dates, cuddles on Richie’s large couch and sex in his California king sized bed, Eddie getting more and more comfortable with the lifestyle Richie leads.

Bill makes the decision to go back to Maine for the weekend, his younger brother broke his arm pretty badly, and he wants to be closer to him to help. Beverly invites Ben over to spend the weekend with them, one less person in the apartment means she can have more quality time with her boyfriend.

Rather than third wheeling the couple the entire time, Eddie spends a few hours with them hanging out like they usually do, before texting Richie, asking if it’s a good weekend to stay with him. The answer is obviously yes, Richie would drop everything to spend time with Eddie, not that he’d admit that out loud to anyone other than Stan and Mike. 

Eddie packs an overnight bag, he’s slowly learning he doesn’t need to pack up his entire room and some to be prepared for a two night stay, especially now because he has some personal hygiene stuff already at Richie’s apartment, but he still ends up with a small suitcase and backpack. 

Richie offers to get him an Uber but Eddie declines, he likes being able to take the subway, as gross as it can be sometimes, it’s nice to have a no traffic ride under the city, leaving his college town and ending up in a nicer uptown area where Richie’s apartment is.

At this point the doorman knows who Eddie is, tipping his hat as he lets him inside without an issue, he’s seen him multiple times with Richie by his side. Eddie waves hello and flashes a smile as he walks in, straight to the elevator to the top floor. 

Eddie opens the unlocked door and toes off his shoes, placing them on the shoe rack by the door, straightening Richie’s as he does his own, before sprinting to the large couch in Richie’s living room. Richie grins and grabs his ankles, pulling him until he’s in his lap.

Eddie lifts himself up and wraps his arms around his shoulders. “I hate that you keep the door unlocked.” 

Richie rolls his eyes, “I lock it at night, and didn’t want to get up to let you in.” He presses a kiss to his temple.

Eddie hums and turns his head to kiss his lips gently, “mmhm, okay.”

“You’re with me the whole weekend?” 

Eddie grins, nodding, “Yes! No work at all, I have some assignments I need to work on that are due Sunday night or Monday in class, but other than those I’m free to be with just you, the whole weekend.”

“Oh wow, I just wonder how we’ll spend this extended amount of time together.” He moves his hands up to his thighs, squeezing gently.

Eddie dips his head down, touching his nose to Richie’s, “oh yeah, it’ll take so long to figure out what we can do with all this free time.”

Richie grins and lifts his head up a bit to kiss him, shifting so his arm wraps securely around his waist. Eddie hums, shifting to press closer. Richie’s grip tightens around him, dipping him down so he’s on his back, pressing his knee between Eddie’s legs.

Eddie tips his head back and lets out a small whimper, earning a laugh from Richie. “so easy.” 

Eddie turns his head away, “am not, shut up.” He pushes at his chest.

Richie rolls his eyes, “please, kitten I know all your spots, I can get you to be a puddle in my hand with a few simple moves.”

“You know nothing about me.” Eddie says firmly.

Richie tips his head down and nuzzles into his neck, kissing softly. “That’s nothing, you’re doing nothing- ah.” His eyes roll back and Richie laughs.

“So easy.” He says again.

“Shut up and kiss me.” Eddie grumbles, threading his fingers in the hair at the nape of Richie’s neck.

Richie does as told, kissing him deeply, pushing his hand under Eddie’s shirt and pinching his nipple to watch him squirm.

Eddie gasps into Richie’s mouth, pressing closer to him. Richie takes his hand back and unbuttons his pants, taking his time to push them off Eddie’s legs, taking his socks with it.

“Tell me what you want, baby.”

Eddie whines against his lips, “want you, touch me.”

“Be specific or you won’t get anything at all, tell me what you want.”

“Fingers, I want your fingers.”

“Good boy.” Richie praises, pulling back to reach in the end table and pull out the small bottle of lube he’s been keeping there since Eddie’s been coming around more often.

He pops open the lid and coats three fingers, taking his sweet time. Eddie tries to stay still, his eyes focused on Richie’s hands, licking his lips as he warms the lube between his fingers. 

Eddie whines, “it’s good enough, daddy, want your fingers now.”

Richie grins, “needy, needy.” He hums.

He turns Eddie around, spreading his legs before pressing the tip of his finger to his hole, watching his face as he pushes all the way in.

Eddie tenses up for a moment before forcing himself to relax, Richie’s hands are much bigger than his own, one of Richie’s fingers is a finger and a half of his own. Richie’s other hand lands on his thigh, squeezing gently.

Richie takes his time, teasing him, enjoying the way Eddie forces himself to stay still, acting like the slow pace isn’t bothering him, how it’s been almost a few minutes and they’re still on just the one finger.

He waits until Eddie whines before pushing in the second finger, spreading them inside of him. Eddie groans and bucks his hips up on instinct, tipping his head back, letting Richie have his way with him.

“Good boy.” Richie praises, moving his fingers a bit faster, giving Eddie what he wants.

He shifts the angle a bit, waiting until Eddie lets out a loud groan, knowing he’s found what he’s looking for. 

After adding a third finger he wraps his hand around Eddie’s cock, jerking it in time with the movements of his fingers inside him, it doesn’t take long until he comes in his hand. 

Eddie lays back with his eyes shut, breathing heavy, he takes a few moments to catch up before pushing himself to sit up, “okay, my turn.”

Later that night, the two of them are curled up together on Richie’s bed, watching some animated movie with little plot, Eddie recognizes the characters from the Angry Bird phone game. They went out to dinner a few hours earlier, Richie taking him to yet another expensive restaurant. 

Eddie traces shapes on Richie’s stomach through his shirt, drawing little hearts and stars. “Hey, Rich?” 

“hm?” He looks down.

“How can you afford to keep me around, I mean you pay for every date, and you’re not cheap with the places we go, and you give me allowances and date bonuses, like, does stand up really pay that much?”

Richie chuckles, shaking his head, “I don’t only do stand up, it’s my main thing, but not the only thing I do, or have done. I wrote for Saturday Night Live for a while, and I’ve done different movies, mostly stupid animated movies, like this one, I voice an angry bird.”

Eddie stares out in front of him, blinking twice before quietly asking, “excuse me?”

“Yeah, I’m some king bird or whatever.” He picks up the remote and rewinds until he finds the character he voices, pressing play and letting Eddie hear his voice come from the beak of an animated bird.

“Richie, what the fuck?” 

“I don’t think you realize how famous I actually am, babe, people pay a lot for my voice.”

“I guess I don’t.”

They wake up the next morning and fool around in bed for nearly an hour and a half until Eddie feels too gross staying in bed for too long. Richie lets him slip into the shower while he goes downstairs to make them a proper breakfast.

He’s placing two over easy eggs and freshly buttered English muffins on a plate for Eddie as he walks into the kitchen, wearing one of Richie’s big shirts.

“Nice shower?” Richie asks, making his own plate.

Eddie nods, “great shower, I feel much better.”

“Good.” He presses a soft kiss to Eddie’s temple as he sits next to him.

They sit in a comfortable silence as they eat breakfast, Eddie swinging his right leg around to hook around Richie’s, getting close to him. Richie smiles into his food, before shaking his head to get the domestic thoughts out, reminding himself that he’s just Eddie’s sugar daddy, nothing more.

“So, you said school’s going well, and the bakery is too, how’s everything else?”

Eddie hums, “pretty good, if I’m not with you I’m with my friends, and that’s nice, especially since they live with me, well, Ben doesn’t but he basically does, he might as well move in at this point.”

“Yeah, so you’re not seeing anyone?”

Eddie looks up at him, confused, “what?”

“I asked if you’re seeing anyone, like, dating anyone.”

“You? I’m seeing you.” He says, as if it’s the most obvious thing in the world.

Richie gives him a blank stare as he processes what he says, realizing that the entire time they’ve had their arrangement, Richie is the only person Eddie’s been with.

Eddie shifts, suddenly uncomfortable, “well, are you seeing any-”

“No!” Richie cuts him off, maybe a little too quick. He clears his throat and shakes his head, “No, I’m only with you, too.”

Eddie smiles a bit, “yeah?”

“yeah.” He nods, a smile of his own growing slowly.

Eddie ducks his head, “good.” He whispers quietly, so soft Richie almost misses it. Almost.

Eddie sits curled up in an armchair in Richie’s now clean office, with his laptop on the coffee table next to him, calculator open in his hand, working on his statistics homework. They picked up the office together a few weeks earlier, Eddie couldn’t handle being in Richie’s apartment knowing there was a room as cluttered as that one. 

Mike and Richie are having a meeting at Richie’s desk, the two of them arguing over business related issues. 

“I don’t have any new material, I’m not going to go around the country giving the same speech about how I fuck your mom, Mike.”

Mike rolls his eyes, “Beep beep Richie, my parents are dead, necrophile.”

“Yeah, yeah, whatever. I’m done with it, I’m sick of touring, I miss my apartment, and I have nothing new to give the poor fucks that find their way into the audience, I’m over it, I don’t want to tour anymore.”

“You can’t just not tour, Richie, that’s your whole career.”

“Is taking a break such a bad thing?” Eddie speaks up, setting his calculator down, “I mean, I don’t mean to stick my nose in things that aren’t my business, but is it really so terrible to take a few months off.” 

Mike rubs his face, “a few months off, aside from the couple shows we already have booked, wouldn’t be terrible. It’s also not great, he’s on a roll right now, getting the recognition he deserves from this business, but we can pick it back up if you really aren’t happy with the material you have.”

Richie sits back in his chair, “thank you. We’ll do a tour or something when I have to film the new special in a year.”

Mike scratches his head, “yeah, I can make that work. This still means you have to do the shows we have booked, there’s three, all within the next couple months, then you can drop off the face of the earth for all I care.”

“Fine, I can do those shows.” Richie stands back up, making his way to where Eddie’s sitting, squishing himself in the small amount of free space on the arm chair, and pulling Eddie into his lap.

Mike sighs and shakes his head, “I’ll run this by with the others, but it should be okay. A tour will be planned out for less than twelve months from now, I suggest you start writing material you’re proud of now.”

Richie nods, pressing his nose to the back of Eddie’s neck, “I will.”

“Good, I’ll see you around, Rich.” Mike stands up and lets himself out.

Eddie frowns, shifting in Richie’s lap to wrap his arms around him, “you know he’s just trying to help with your career.” He says softly.

“I know, I know. I’m being unreasonable.”

“It’s not that, you have reason to not want to tour, and overwork yourself, but Mike has a point about having momentum right now, you’re going to take a hit.”

Richie nods, “yeah, yeah. Can we not talk about this right now? I don’t want to think about it anymore.”

Eddie hums, “how about you give me twenty minutes to finish this assignment, and I can help you not think about this anymore.”

Richie smiles a bit, “yeah, sounds good, but I’m not moving.” 

Eddie wakes up the next morning with Richie’s body wrapped completely around him, he closes his eyes and breathes in his scent. He doesn’t think he’s ever felt more comfortable and relaxed in his life.

He lets himself stay like that for a few moments when Richie shifts, pressing his dick against the curve of his ass, and Eddie is suddenly very aware of his morning wood. He doesn’t even attempt to stay still and let Richie sleep, instead he shifts and rubs his ass against Richie’s dick, seeing if he can wake him up.

Richie’s hand moves from his waist to his stomach, pressing him closer to his chest, leaning down to nuzzle his neck, “well, good morning to you too.”

Eddie tips his head to the side, letting Richie have better access to his neck, feeling him begin to suck a hickey by his ear. He shuts his eyes and lets out a soft moan, placing his hand over Richie’s.

Richie pulls back after a minute, satisfied with the mark he’s made, it’ll darken with time, but for now it’s a pale red.

He rolls Eddie onto his stomach and kisses down his back, “how are you feeling, still sore?” 

Eddie shifts, “yeah, just a little, sorry.”

“you don’t have to apologize.” He nips at his shoulder blade, “but if you’re up for trying something new, I have an idea.”

“I’m always up to try something.”

Richie grins and pulls back, grabbing the lube they used the night before. He sets it next to Eddie and pulls him up, manhandling him until he’s on his hands and knees. Eddie strains his neck to look back at him, a little confused on what he’s doing, but trusting him enough that whatever Richie does, he’ll enjoy.

Richie pops open the bottle of lube and pours some onto his hand, “this might be a little weird, but you’ll like it, I promise.”

Eddie spreads his legs a bit wider and Richie coats the inside of his thighs with the lube, using his hand to slick up his cock. He pushes Eddie’s thighs back together, getting on his knees behind him, his hands on his hips.

“Keep your thighs together, and stay still.” He says, firmly.

Eddie nods, “okay, Daddy.”

“Good boy.” Richie praises as he sets himself up behind him, slowly pushing his cock between his thighs.

Eddie gasps, dipping his head down, he wasn’t sure what exactly Richie was doing, but now it’s clear, he’s using Eddie’s slicked up thighs like a toy, keeping Eddie’s hips still, and legs pressed together like a toy for his own pleasure.

Eddie groans and tries to push back, Richie’s hands grip him tighter, keeping him still, “I said stay.”

“Sorry, Daddy, I’ll be good.”

Richie slides out and pushes back in harder, able to pick up the pace much quicker, not worrying about hurting Eddie as much. His cock slides against Eddie’s and he hears his high pitched moan, feeling his muscles strain as he forces him to stay still.

“Good boy,” he grunts, dipping his head down by his ear, covering Eddie’s body with his own.

Eddie tips his head back and bares his neck for Richie, “D-daddy, it’s so good, go harder.”

Richie slams his hips back, Eddie’s moans as motivation to keep going as hard as he is. His hand slips under Eddie’s body and wraps his hand around his cock, stroking it less than four times when he comes, splattering his own stomach.

Richie pulls his hand back, grabbing his hips once again, using him for his own pleasure, thrusting a few more times before coming while he’s pressed against his ass.

He stays draped across his back for a minute, catching his breath. Eddie slumps down, pressing his face into his pillow and closing his eyes.

Richie rolls off of him, onto his back, resting his hand on his stomach, closing his eyes.

Eddie takes deep breaths, lifting his head out of his pillow, “you were right, I liked that a lot.”

Richie turns his head and presses a soft kiss to Eddie’s shoulder. “I thought you would, baby.”

The next Monday Richie finds himself sitting alone at his kitchen table, picking at the eggs he made for himself. His apartment feels empty without Eddie there, having gotten used to having him around the entire weekend, he can’t help but feel a bit lonely.

His phone buzzes with a snapchat from Eddie that he opens almost embarrassingly fast. He’s met with a bored looking selfie of an adorable face. 

Richie’s eyes can’t help but be drawn to the uncovered dark red mark placed under Eddie’s ear. He feels a flash of possessiveness strike through him and stares at it until the pictures times out and he’s met with the white contact screen.

He shakes his head and says, “you’re just his sugar daddy.”

Their next date is dinner at a nice restaurant outside of the city, by this time Eddie doesn’t feel awkward or out of place at all, that may be because he researched proper etiquette when at such a nice restaurant, which forks and spoons to use for which dish, how to properly have the napkin.

Richie on the other hand doesn’t care, and it clearly shows, he uses his dinner fork for his salad, and his soup spoon to scoop ice cubes out of his water to crunch on before the appetizers arrive. 

As their entrées arrive Eddie’s passionately talking about the shift he picked up the night before at the bakery.

“I never work the closing shift so I barely knew what I was doing to begin with, but it was a quarter to nine, I had just finished wrapping everything in the bake case and turned off the light when some woman came in and ordered three cheesecake slices, all different kinds, and then had the nerve to get upset with me when I packaged them to go instead of putting them on plates! When I explained to her that it was literally fifteen minutes to closing and we stop doing for here orders an hour before nine, she yelled at me! I had to go grab one of the owners that was closing with me to deal with her. I do not get paid enough to deal with customers like that, I’m just a cashier at a bakery, I don’t have any authority there.”

Richie shakes his head, “fuck that lady, if I were you I would have shoved my foot so far up her ass my shoe laces would come out of her mouth.”

Eddie snorts, covering his mouth and shaking his head, “I fucking wish I could do that, but I need that job, so I can’t.”

“How much do you get paid there?”

“I got a raise a few months ago, so fifteen dollars and twenty-five cents an hour. I try to get thirty hours a week, but usually I only end up with about twenty, I pick up shifts where I can though.”

Richie hums, and they move on, changing the subject to the weird man he saw on the subway with Stan that morning, hearing Eddie laugh as he reenacts the way the man blatantly flirted with Stan, despite the obvious ring on his finger, is the highlight of his day. 

Richie drives him back to his apartment that night, taking the long way back so they can talk. Talking turns to Eddie vaguely listening to him rant about the business side of comedy, and that turns into him not listening at all, stretching the seatbelt as he leans over, placing a hand on Richie’s upper thigh. 

Richie stops mid-sentence; his eyes turn dark and voice deep. “Eddie, baby boy, I’m driving.”

Eddie looks up at him with his big brown eyes, almost pouting. “There isn’t anyone around, please, daddy?”

Richie bites his bottom lip before he nods, “hand job. Nothing more, keep your mouth far away from my dick.” Eddie pouts and Richie rolls his eyes, “such a cock slut, you can suck me off when I’m not driving.”

Eddie grins and unbuttons Richie’s pants, slipping his hand under his briefs and pulling out his cock. He pulls his hand back to lick his palm, getting it slick before jerking him, starting slow, wanting to make this last.

Richie keeps his eyes on the road, he has this route memorized by now, they go out of the city for dates like this pretty often, Richie could do this drive blindfolded if he had to. He curses softly when Eddie’s thumb swipes the tip of his cock, he sits further back in his seat, giving Eddie as much room as he can in the small amount of space between his legs and the steering wheel.

“Good boy, fuck, so good with your hand, baby.” Richie groans.

He twists his hand on his cock, using his precum as lube as he picks up the pace, moving his hand faster as he feels Richie get closer. He can always tell when Richie is close, he talks a lot, it’s hard to get Richie to shut up on a normal day, but near impossible when he’s about to come.

Richie pulls into the parking garage for Eddie’s building and parks in the one spot they have saved for their apartment, no one living there has a car, they couldn’t afford one if they even wanted one.

Richie turns his head, placing his hand on the back of Eddie’s neck, pulling him in for a deep kiss as he comes in his hand, moaning soft praises in his mouth.

Eddie pulls back after a minute and licks his hand clean, before he pulls out the hand sanitizer he keeps in Richie’s glove compartment and cleans off his hand.

Richie sits back and takes a few breaths before reaching out. Eddie shakes his head, “no, I have to be up early, and if we do anything now it’ll take forever for me to get up there and go to sleep.”

He leans in for one last kiss, and leaves Richie’s car. Richie tucks himself back into his pants and shakes himself back to reality, making a mental note to pay Eddie back for that, some way or another.

The next morning Eddie checks his phone as he gets ready for work, seeing a notification from his banking app, two deposits have been made five hundred with the note “date” along with eight hundred labeled “raise in allowance”.

Eddie immediately calls Richie, not worrying about waking him up so early in the morning.

“Kitten, it’s five am.”

“What the hell, Richie! This is way too much, we agreed, three hundred a date, and five hundred for my allowance, this is so much money, there is no way I can accept this, you’re spending so much on me!”

“Google my net worth.” Richie hangs up.

Eddie huffs, googling ‘Richie Tozier’s net worth’ just to see what he was talking about, since Richie thought that was a way to end the conversation. His eyes go wide as the screen finishes loading, the number in big bold letters against the white background.

Richie Tozier is worth twelve million dollars.

Eddie types out his two weeks while he’s on the subway to work, he doesn’t need the job anymore, not when Richie’s paying him more than enough for rent and every other bill he has. Now, he’s able to put all his energy into his schoolwork.

When Eddie’s spring break rolls around, Richie has a show date in Pennsylvania, not wanting to miss out on spending extra time with him, he makes it a mini vacation, bringing Eddie along.

Eddie doesn’t travel much, he never went on family trips as a kid, the longest he’s ever travelled was the drive from his hometown in Maine, to his school in New York. Flying there is the first time Eddie’s ever been on a plane, Richie laughs at the mask he wears, but Eddie gives him a ten-minute lecture on airborne diseases, and how an airport is a big breeding ground for bacteria.

Stan and Mike hold back their laughs as they banter almost the entire way, fighting over what movie to watch on the way there, even though they have separate movie screens on the seats in front of them.

Richie pokes fun at Eddie packing snacks and sandwiches for them, he refuses to pay twelve dollars per sandwich when he made these perfectly find peanut butter and jelly sandwiches in the comfort of his apartment for way less than that, telling him that just because he can afford it, doesn’t mean he should make unnecessary purchases. 

Eddie watches the show from backstage, even if he wanted to be in the crowd, the show was sold out, there isn’t a seat for him. He stands next to Mike, where he’s typing on his phone, taking notes about the show, writing which jokes hit well with the crowd, which ones aren’t as great, and which ones Richie’s the most confident delivering. 

Half the show Eddie is in tears, bending over and covering his mouth so he doesn’t laugh too loud. Every so often Richie glances backstage and sees Eddie hunched over, body shaking with uncontrollable laughter, and grins wider, as long as he can make Eddie laugh like that, he’ll tell his stupid jokes all night.

At the end of the show, Richie hooks the mic back up to the stand as he says the punchline to his final joke, then thanks the crowd as they laugh, backing up and waving with a grin.

He walks backstage, his smile growing where he sees Eddie curled in on himself, laughing so hard he’s in tears. Mike talks with him for a minute, sharing his notes before letting him go, put an arm around Eddie and pulling him up, kissing his cheek.

“How’d you like it?”

Eddie rubs his eyes, smiling up at him, “I loved it, seeing you preform, you looked so happy, plus you’re fucking hilarious.”

Stan touches Richie’s shoulder, “not to break this up, but we should head out, you’re sweaty, and we want to beat after show traffic.”

After a quick shower the four of them end up in the bar on the first floor of the hotel, Eddie nearly on Richie’s lap as they sit in the booth. Richie orders him a fruity cocktail to sip on, but he’s more concerned with chewing on the straw as he watches the way Richie’s throat moves as he talks to Mike.

Stan slips away after a bit, turning in early to call his wife before bed. Eddie pushes his half-drunk cocktail to the side and leans on Richie’s shoulder, waiting for a break in their conversation to press a soft kiss to his cheek, leading to his lips.

Richie smiles into it, indulging him for a few moments before pulling away, only for Eddie to whine.

Mike makes a face and shakes his head, “That’s my cue to leave, night boys.”

Richie laughs and puts his hand on Eddie’s waist, “c’mon baby, us too.” He slides out of the booth and takes Eddie to the elevator.

The second the doors shut, Eddie’s standing on his toes to kiss him, when Richie tips his head back he presses soft kisses to his neck, rubbing his nose on the stubble, sighing happily.

Richie all but drags him to their room, Eddie wrapped around his arm, refusing to let go. He manages to get the two of them on their bed, Eddie pulled into his lap when he can finally give him a proper kiss.

“Clingy today, aren’t you?”

Eddie hums, “you were great on stage.” He wraps his arms around Richie’s shoulder’s, “it was hot, you’re hot.”

Richie kisses him softly, “thank you.”

“I mean it, whenever I wasn’t laughing I was thinking about how I couldn’t wait to get you in bed like this, you looked so good, your stupid Hawaiian shirt wasn’t buttoned, kept thinkin’ I should have left a hickey, where everyone could see it.” He dips his head to press kisses at his neck, moving the collar of his undershirt.

Richie tips his head back, letting him have a bit more room, “I don’t think anyone would have cared.”

Eddie snaps his head up, “what? You’re kidding right. I could count four people in the front row alone that were giving you specific looks the entire show, plus not to mention you have a thirst following on twitter.”

Richie tilts his head, “I guess I don’t pay that much attention.”

“Well, I do, and I don’t like to share.” Eddie huffs.

Richie flips them over, nuzzling his face in his neck, “good thing I’m not looking for anyone else.”

Eddie grins, pushing his hands under Richie’s shirt as he presses kisses to his neck. The rest of the night is full of soft kisses and sweet noises, Eddie wrapped completely around him, mewling quietly as Richie does everything he knows he likes.

The next morning Eddie wakes up to Richie pressing soft kisses across his face, whispering pet names. They stay in bed for most of the morning, sharing soft touches and sweet kisses, until their hunger gets uncomfortable, and they order room service.

They eat their breakfast in bed, Richie feeding Eddie half of it, just because he can, giving him kisses between each bite to see Eddie’s playfully irritated face, with a smile behind his eyes. 

A few weeks later, Eddie follows Richie into his bedroom, they had just come in from a date across down, a high-end seafood restaurant, where Eddie got to eat as much shellfish as his heart desired, after the previous week of school work he deserved to let himself indulge.

Richie settles on his bed and pulls Eddie into his lap, pressing a soft kiss to his lips before dipping his head and kissing his neck, slipping a hand under Eddie’s shirt. Eddie tips his head back a bit, shifting in his lap, he isn’t focused on Richie right now, all he can think about is the three papers he has due in two weeks.

Richie pulls back with a frown, kissing behind Eddie’s ear usually leaves him a whining puddle, but he hasn’t gotten so much as a gasp. 

“Baby, are you okay?”

Eddie looks up, shaking his head to clear it, “yeah, yeah. ‘m fine, Richie.”

Richie slips his hand out of his shirt, resting it on his waist, “you sure about that, Eds?”

Eddie nods, “yeah, I said I was fine, just have a lot on my mind, I guess. School stuff, really. You don’t need to hear about it.” He slips off his lap, getting off the bed. “I’ll just go home, I’m not really feeling sex right now, sorry.”

Richie frowns, reaching out to take his wrist, “hey, you don’t have to leave if you don’t want sex, and you definitely don’t have to apologize for it.”

Eddie glances down at his wrist, watching Richie’s hand. “I don’t want to overstay my welcome.”

“You could never do that, baby. Remember our arrangement wasn’t supposed to be sexual. I don’t need to have sex with you to want you around.” Richie pulls him back on the bed, “stay the night with me.” 

Eddie nods, ducking his head, “okay, I’ll stay.”

Later that night the two of them are tucked into Richie’s bed, watching a bad cartoon movie on his flat screen. Eddie’s curled into his side, he was able to properly rant about how school is going, how behind he feels as they near the end of the semester, how he has final papers, on top of final projects, on top of final exams, all he needs to complete within the next couple weeks.

Eddie confesses that he still doesn’t know what he’s going to do over the summer, he doesn’t have a place to go after he cut off his mother before the year started. His friends would be happy to take him in, take him back to their families, but he doesn’t want to feel like an outcast. 

Richie lets him vent for a while, when Eddie’s out of everything and his eyes are watering and sniffling just lightly, he presses a kiss to his hair and tells him everything will turn out alright.

Richie points out characters in the movie they’re watching, talking about the actors and actresses that play them, telling Eddie stories of parties he’s been to, where those men and women would make absolute fools of themselves.

It has Eddie laughing with near tears in his eyes as Richie recounts the time Andy Samberg made the top floor of their hotel into a slip ‘n slide and crashed into somebody else’s room, someone who was not happy that they were having a floor party.

Richie falls asleep first that night, Eddie resting his head on Richie’s chest. His head swims knowing just how famous he is, telling stories about known comics like they don’t attend high profile events and award shows. 

He snuggles his face into Richie’s neck, pressing a soft kiss to his chest before letting himself fall asleep in his arms. 

The next morning Eddie slips out of bed before him, making coffee and a proper breakfast before Richie walks into the kitchen. He stays a bit longer than he told himself he would, indulging himself in sweet kisses and multiple pieces of toast with the special farmers market jam Richie keeps in his fridge just for him, since he’s stated on multiple occasions that it is disgusting, but somehow whenever Eddie finishes the jar, a new one magically appears in the fridge the next time he’s over.

Eddie stands on his toes and kisses Richie goodbye before he opens the door, “Thank you, seriously. Last night made me feel a lot better.”

Richie smiles, “no problem, kitten. I’d do it anytime for you, next time you’re having a day like that just tell me.”

Eddie smiles at him, kissing him again before shutting the door. He walks out of the building and to the subway, sitting on the train he thinks about how sweet Richie was to him, and Eddie would do the same for him, of course he would he loves him.

Sitting up straight and staring at the empty seat in front of him he repeats the words in his head over and over again.

He’s in love with Richie Tozier.

Fuck.

Eddie storms into his apartment, making a beeline for Beverly’s room, opening the door without warning. Bev sits up in her bed, pushing her laptop off her lap, opening her mouth to question what the hell Eddie’s doing in there.

“I’m in love with Richie Tozier!” He yells.

Beverly’s shoulders relax, “yeah, buddy, I know that.”

Eddie looks taken aback for a moment, “w-what? No, you can’t know, I just found out!”

“Oh, well, catch up, we’ve all known for a while.” She sits back, pulling her laptop closer to her.

Eddie steps closer and shuts her laptop, ignoring her noise of protest. “there is no way you could have known! It’s about me, and I just found out, wait. What do you mean ‘we’ve all known’? Who is we?”

Bev rolls her eyes, crossing her legs as she sits in bed, “It took Bill a hot minute, but Ben and have known since you came home after you had sex with him for the first time.”

“that was so long ago, like, literal months ago. You knew I felt this way and didn’t tell me?”

“In my defense, I didn’t think I had to explain your own feelings to you, Eddie.”

Eddie groans and lays back, “well, what the fuck am I supposed to do now? I’m in love with my sugar daddy!”

Beverly shrugs, “what do you want to do?”

Eddie rolls onto his stomach, shoving his face into her comforter. He doesn’t answer.

The end of the semester rolls around, Eddie got amazing grades on his final projects and papers, making it onto the Dean’s List for the first time since he started college, he knows he has Richie to thank, now that he isn’t occupied with two jobs, he was able to give his schoolwork the proper amount of attention.

Everyone packs up their belongings and heads back to their hometown for the summer, except for Eddie. Bill overs his home to him, saying his parents and brother would love to have someone join them, and he knows that’s true.

Beverly does the same, her aunt calling him personally to offer him the spare bedroom. He declines them all, even Ben’s promise of a big cuddly dog to sleep in his bed.

In the end, he feels that it would be intruding on their families, no matter how many times they tell him he’s more than welcome. Eddie brings it up to Richie one night, while they’re lying in bed together. 

On impulse Richie asks him to spend the summer in New York, with him in his apartment. He takes a deep breath, ready to defend his argument but Eddie looks up and accepts before either of them can fully think it through.

Richie grins and dips his head down, now he doesn’t have to worry about what he’d do for three months without Eddie around to keep him company.

A month into their summer break Eddie finds himself sitting alone in their bed, Richie left a few hours ago to have a meeting with Mike across town, finalizing tour dates, and a specific show to film his new special.

He pulls out his phone and facetime Beverly, she answers fairly quickly, her pixelated face lighting up his phone screen, Ben sitting next to her, his face half cut off, but seeing even part of him makes Eddie grin.

“Hey, there, Eddie!”

“What’s up? How’s Ben’s family?”

“Great! Everyone is really sweet, he’s coming home with me next week, he gets to meet my aunt for the first time.”

Eddie grins, genuinely happy for the two of them, “that’s great, Bev!”

They talk, just the three of them for a while before patching Bill in for a three-way facetime call, grinning when he’s successfully answered the call.

The four of them banter for a while, talking about as much as they can over everything that’s happened over the summer. Ben tells them about the trail he’s been running with his dog every morning, Bill talks about the little projects Georgie has gotten him to build, Bev talks about her Aunt, and how nice it is to be around family for the first time in a while.

Eddie talks about the things he’s done and places he’s been with Richie, a fond smile on his face as he tells them about their trip to the zoo.

“Damn, Eddie, you’re really in love with this guy, huh.”

Eddie groans, rolling onto his stomach, “yes, I am, I’m so in love my heart hurts, but there’s nothing I can do about it. He’s so famous, with all of these famous friends, if he wanted a relationship he could set himself up with someone who understands that life, not some kid still figuring out who he is.”

“Just confess, Eddie,” Bill speaks up, “I mean, what’s the worst that could happen?” 

“well, for one thing I could lose the current place I’m staying at, and also my current source of income, since my financial situation entirely depends on him.” He says a little harsh.

Bill sinks back and Bev shakes her head, “no, you’re just a coward.”

“Hey-”

“I mean it, Eddie. If this goes south you can spend the rest of the summer with one of us, our families would love to have you around, and I know Richie has been giving you more than rents pay, you have enough saved that’ll hold you over until you can find another job the way you had before.”

“Fuck you, Bev. I’m not afraid of any of those things, they’re all material, I’m afraid of losing Richie.” He’s in love with him, the thought of rejection is ten times worse than being homeless or broke.

Ben sighs, “Eddie, if you’re really all in for Richie, you have to tell him.”

Eddie rubs his face, “I know.” He says quietly, and hangs up.

He rolls onto Richie’s side of the bed, pressing his face into his pillow, breathing in the smell of his aftershave as he falls asleep.

Eddie wakes up to Richie peppering kisses across his face. He slowly opens his eyes and turns his head for a proper kiss.

“Morning sleepyhead, it’s almost four in the afternoon.”

Eddie smiles, watching Richie’s face, his heart feels full being so close to him, feeling Richie’s stubble across his cheeks, being able to see the light freckles on the bridge of his nose, he can’t help it, the words are coming out of his mouth before he even realizes it.

“I love you.”

Richie freezes, he swallows hard and pulls back, standing up straight.

Suddenly Eddie is wide awake, he sits up on the bed, rubbing his face, shifting to get up, “Fuck, fuck, I’m sorry, I fucked up. I’m sorry, I’ll just go.” He says quickly, throwing his legs over the side of the bed, moving to stand up when Richie puts a hand on his chest to stop him.

“No, just.” He pauses, taking a deep breath. Eddie looks up at him with big, fear filled, eyes, “please, don’t say it, if you don’t mean it.” His voice is small, quieter than Eddie’s ever heard before, he sounds like a scared kid.

Eddie relaxes his shoulders, his eyes soften and he nods, “Rich, I meant it.”

Richie stares at him for almost a full minute, processing those three words for a long time. Eddie begins to get nervous again, shifting on the bed, he clears his throat. “uh, do you want me to-”

He’s cut off by Richie bending down and kissing him, hard. It takes Eddie a moment to figure out what’s happening, before he kisses back, a grin breaking out and almost making it too difficult to kiss. He wraps his arms around Richie’s shoulders, pulling him down.

Richie breaks the kiss to rub their noses together, “I love you, fuck, I love you, so fucking much.”

Eddie can’t help but laugh, and kiss him again. Richie climbs onto the bed and scoops Eddie into his lap, holding him as close as he can, breaking the kiss again to hug him tucking his face into his neck, mumbling soft, “I love yous” over and over again, while Eddie tangles his fingers in his hair.

It takes a while, but Richie lifts his face back up, kissing Eddie again, “you mean this, right? Like, you love me love me?”

Eddie cups Richie’s face, looking him in the eyes, “Richard Tozier, I am so beyond in love with you, I mean it in every sense of the word.”

Richie grins again, “Fuck, you’re perfect, I love you too.” He leans up and kisses him again, rolling them over in the bed, Eddie squealing with laughter.

Months later, Eddie finds himself backstage while Richie is performing his brand-new standup, his first show before the tour. He stands next to Stan and Mike as he watches his boyfriend walk around the stage, playing with the microphone cord as he tells his jokes.

“So, some things happened while I was gone, that I suppose I’ll address. Everyone knows my dirty little secret, surprise! I’m a huge homosexual, and on top of that, I have a sugar baby! Literally, a sugar baby, my boyfriend is still in my phone as sugar baby, and I refuse to change it, no matter how many times he tells me to, I won’t do it!”

Eddie rolls his eyes, “beep beep, Richie.” He says to himself, but the fond smile on his face could light up a dark room for hours.

**Author's Note:**

> Please comment and kudos i run purely on caffeine and attention  
> You can contact me at [my tumblr minthalo](http://minthalo.tumblr.com/) I'd love to make new friends in this fandom!


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